Synthesis of new 1H-1,2,3-triazole-1,4-naphthoquinones

Abstract

In this work, were synthesized new 1H-1,2,3-triazole-1,4-naphthoquinones via 1,3-dipolar cycloaddition reaction using CuI/acetonitrile without addition of base or ligand. The compounds (3a-i) were obtained in moderate-to-good yields 45-92%. To prepare (3d), we obtain a mixture of (3d) and (4) in a ratio 3:1, that it was difficult to separate. The low yield for the compound (3f) can be also justified based in the formation of aminonaphthoquinone (4). The acetylation of (3h) and (3i) afforded the compounds (5) and (6) in 77% and 35% of yields, respectively. The low yield of (6) was due to formation of 35 % of the elimination product (7).

Keywords

• 1,2,3-triazole
• 1,4-naphthoquinone
• cycloaddition